How do I dress to look good yet stay warm when going to parties in the fall/winter?

I think leather looks a little trashy personally. Why not a nice wool mini with tights. A gray skirt and tights that pick up the pink in the sweater would be awesome on you I bet. And again, I think ankle boots with a small heel (2-3 inches) look better with a mini-skirt than knee high stiletto boots. But I agree they won't be as warm. You could wear a long coat with a colorful scarf.